Data: A Love Story by Amy Webb

Hacking her way to a hirsute husband

Writing in the years before online dating’s boom, Alain de Botton opened his debut novel On Love thus:

“The longing for a destiny is nowhere stronger than in our romantic life. All too often forced to share our bed with those who cannot fathom our soul, can we not be forgiven if we believe ourselves fated to stumble one day upon the man or woman of our dreams? Can we not be excused a certain superstitious faith in a creature who will prove the solution to our relentless yearnings?”

So it is that author and consultant Amy Webb defines the romantic search described in her memoir Data: A Love Story as a quest not for just a life partner … but a soulmate.

At the start of her tale, Webb’s writing career as a journalist for Newsweek has brought success, adventure and international travel, but no real romantic prospects for the long term. On the cusp of a move home from Japan, she meets an attractive man who shares her U.S. and Asian connections, and they soon begin an ill-fated romance.

Not that things crumble immediately. It’s not until they’ve moved stateside together, and rented an apartment in Philadelphia, so he can attend law school, that things begin to decline. The couple mostly ignores their problems until one day when Webb decides to discuss their relationship. She finds herself summarily separated, asked to move out within days (likely, she learns later, to make room for a new love her companion had secretly begun seeing).

Webb turns to the Internet for new romantic prospects. By now she’s entered the biological minefield of her 30s. She’s also working for herself—a choice that brings professional fulfillment but reduces chances to meet men.

Her relatives do their best to set her up with any and all single chaps of their acquaintance (mostly the weirdos one expects in a tale like this). Even so, Prince Charming doesn’t seem to share her ZIP code or social circles.

As the entrepreneur of a startup and an ardent fan of the British writer Nick Hornby, Webb devotes a few precious “units” of her day to setting up the requisite online profile. She culls quickly through the photos on her hard drive and cribs a few paragraphs and bullet points from her resume.

Despite the work-heavy nature of the resulting profile, Webb soon commences a lengthy and predictably disappointing series of dates (her philosophy at this point: accept all comers). While other online daters in those days start anonymous blogs recounting their love-life travails, Webb instead chooses to track hers in a spreadsheet she secretly updates during bathroom breaks on her dates. The highlights—or lowlights, as the case often proves—she emails to a small circle of friends and family.

Among the uninspiring dozens, Webb meets liars, high-fivers and a shameless pot-smoker who sticks her with the bill for a pricy dinner.

Eventually, though, our heroine has an alcohol- and nicotine-fueled epiphany. It results in a 72-point list of things she wants in a man. The unexpurgated details appear in the book.

Her criteria range from financial acumen to sexual prowess and body hair … and include a dislike of Cats the musical. (A previous boyfriend played the soundtrack frequently.)

Eventually she develops a complicated weighting scheme for dating. Her ideal man would score 1,500, with 700 points her first-date minimum requirement. (Not even this reviewer, a one-time “diff EQ” student, could quite figure out the math on this.)

Despite the caddish nature of her ex, she lists mostly physical or behavioral traits among the coveted 72. By my count, a mere 12 desired qualities pertain to character or emotional health. Only one such attribute—“no history of cheating”—made it onto her list of “top tier” traits.

Why mention this? Webb wants happiness from her ideal partner, but apparently this stems more from common interests than shared values, honesty or a willingness to keep one’s word even when inconvenient.

Wait—there’s more. The list entails only one part of a two-prong strategy.

Webb devises to improve her online-dating experience as a way to find “twue love,” so she next turns to prong two—research. To improve her online profile, Webb rejoins JDate . . . questionably.

She signs on not as one, but 10 different men. Through these personas, she interacts with nearly 100 women, all of whom she declines after a few interactions.

After tracking and analyzing numerous components of the women’s profiles and their exchanges with her cyber Trojan horses, Webb retools her profile—and herself—complete with a new haircut, photo shoot and workout regimen with a personal trainer.

Around this point, I started to see Data as better material for a chick-flick (say, starring Tina Fey?) than a credible memoir.

A screenwriter friend once told me that any good story has two conflicts. On the surface, we encounter the external or presenting conflict (boy tries to get on the football team, girl tries to win the big job). Underneath runs the internal, more fundamental conflict (boy longs to win the approval of a distant father, girl wants to rise above a poor high-school image). Take away the subtler piece of narrative and you still have a story, but nothing super compelling.

This explains why Data falls short. The main narrative arc basically consists of Webb successfully adopting a new strategy for online dating, through which she meets her now-husband.

The end.

And yet . . . she hints here and there that she might have written a better, more interesting memoir.

For one thing, while Webb sets the conflict up so that algorithms, a mediocre profile and dishonest men stand as the main obstacles she tries to overcome through her online dating “hack,” neither of two previous long-term relationships involved men she met online.

Only deep in the endnotes does Webb acknowledge the role her own judgment played in those ill-fated romances. Yet even then, she blames those disappointments more on compatibility than any character or judgment flaws—in the men or in herself. Is a cheater more likely to smoke and play Andrew Lloyd Weber soundtracks than he is to lie or keep secrets from you?

A further problem with Webb’s perceptiveness about her romantic woes emerges in the contrast between her 72 criteria and the qualities she hopes to replicate from her parents’ marriage. Though she admires her father’s longsuffering commitment to a wife who endures the disfigurement of cancer treatments, Webb never reckons with how such self-denial and faithfulness square with her own, happiness-driven approach to love and marriage.

Maybe she needed more Rolling Stones songs in her music library. Though I respect the case Webb makes for George Michael fandom—it even convinced me I need to hear some of the songs she mentions—nevertheless the Stones’ “You Can’t Always Get What You Want” offers a wiser perspective on life.

Want and need frequently look very different—and even our understanding of desire can be incomplete.

Take shoes, for instance. I once bought a pair of polka-dotted, high-heeled Oxfords online, convinced I’d found the perfect reward for some recent boon … only to discover that they were poorly made and had very thin soles. Meanwhile, a pair of suede boots I bought mainly because of the 90 percent discount have proven one of my longest-lasting, most beloved pairs. I love them … even though I didn’t initially like their pointed toes.

Or who hasn’t labored over a restaurant menu, only to find that your dinner companion’s entrée looks more appetizing than the meal you thought you wanted? If we can’t even be consistently relied on to choose shoes and suppers, should our judgment in spouses prove any better?

To her credit, Webb does winnow down her exhaustive, 72-point list based on both a personal happiness matrix (albeit defined as “needs”) and the qualities her family would want in her spouse. The list, however skewed, provides both quasi-objective validation of her previous romantic failures and the (mostly) dismal setups her family arranged. Almost none of those men had even the most basic traits Webb and her family agree a husband should have.

If Data falls short as memoir, Webb does a stronger job offering suggestions for the online dater looking to quit growing his or her bad-date anecdote repertoire.

For instance, she recommends keeping most profile answers to three sentences or less and talking very little of work, even if you love your job. She also suggests waiting almost a day before answering messages. Be warned that the bulk of these tips appear well back in the narrative: Flip to chapter 10 and the appendix if you’re truly impatient.

After reading Data, I hemmed and hawed about conducting some personal online ‘research,’ until I finally gave in and logged on to at least compare my deactivated profile to Webb’s suggestions.

This resurfaced my OKCupid profile, where three men who asked me out with nary an introduction. Um, three points for my minor, Webb-inspired edits? Strangers have yet to reprise the most bizarre offers and innuendos men sent the last time I was online (no, I do not help men lose their virginity). Still, I’m not sure I’ll rely on ’Cupid long.

You see, there’s one thing de Botton elides in his description of romantic mystics.

We come in two flavors—those who think Fate’s what you make for yourself … and those holding out for kismet.

Some of us cling to a “… certain superstitious faith in a creature who will prove the solution to our relentless yearnings…”

We are still old-fashioned enough to trust that love arrives through living instead of searching.

Anna Broadway is a writer and Web editor living near San Francisco. The author of Sexless in the City: A Memoir of Reluctant Chastity, Rolling Stone once described her as “fire, brimstone and brains.” She is a regular contributor to the Her.meneutics blog and the coffers of various yarn stores. Find her on Twitter @annabroadway.